The title compound, C13H17NO3, adopts a conformation in which the aromatic ring and the mean plane of the piperidine ring are almost perpendicular to each other [dihedral angle = 79.25 (6)°]. The presence of the carbonyl group alters the conformation of the piperidine ring from a chair to a twisted half-chair conformation. In the crystal, pairs of strong O-HO hydrogen bonds link the molecules into inversion dimers. Weak C-HO interactions extend the hydrogen-bonding network into three dimensions.

Related literature

For the use of related lactams in the synthesis of febrifugine analogues, see: Michael et al. (2006). For information on the biological activity of febrifugine, a quinazoline alkaloid with potent antimalarial activity, see: Murata et al. (1998). For the use of chiral oxaziridines in asymmetric hydroxylation, see: Davis et al. (1990). For the conformation of six-membered rings, see: Boeyens (1978).

Experimental

Crystal data

C13H17NO3

Mr = 235.28

Monoclinic, P 21 /c

a = 12.980 (3) Å

b = 7.6143 (17) Å

c = 12.189 (3) Å

= 90.497 (5)°

V = 1204.6 (5) Å3

Z = 4

Mo K radiation

= 0.09 mm-1

T = 173 K

0.32 × 0.26 × 0.18 mm

Data collection

Bruker APEXII CCD diffractometer

8378 measured reflections

2895 independent reflections

2271 reflections with I > 2(I)

Rint = 0.027

Refinement

R[F2 > 2(F2)] = 0.042

wR(F2) = 0.124

S = 1.08

2895 reflections

158 parameters

H atoms treated by a mixture of independent and constrained refinement

This is an open-access article distributed under the terms of the Creative Commons Attribution Licence, which permits unrestricted use, distribution, and reproduction in any medium, provided the original authors and source are cited.